


Dizzy Daydreams & Drunken Hazes

by billyteddytrash



Category: Supernatural
Genre: Alternate Universe - High School, Broken!Cas, Fluff, Friends to Lovers, Insecure!Dean, M/M, Multi, Pining, Popular!Dean, So much fluff like wow, Teacher!Crowley, hipster!cas, kind of, teacher!Bobby
Language: English
Status: In-Progress
Published: 2013-11-17
Updated: 2014-11-18
Packaged: 2018-01-01 19:14:07
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 1,207
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1047576
Author URL: https://archiveofourown.org/users/billyteddytrash/pseuds/billyteddytrash
Summary: <blockquote class="userstuff">
              <p>There's nothing more intimidating to Dean Winchester than attention from one Castiel Milton.</p><p>He was the ideal crush, all shaggy hair and blue eyes, not to mention totally and completely unattainable. Nothing in the world would get Cas to give Dean even the slightest bit of recognition. Up until the second half of his senior year, he didn't need to worry about any attention from Cas. But for some reason, halfway through January, Castiel starts acknowledging him. Long looks and suggestive smirks, winks for no reason, the whole ten yards.</p><p>When Dean confronts Castiel about the constant distraction, things get a whole lot messier and a whole lot more interesting. With only five months left of high school, what will these mixed signals and long-suppressed feelings lead into?</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Hello! This is the first chapter in a planned 20-chapter High School AU. And those are only the planned ones. My other Destiel fic (I Just Can't Bury You) is pretty serious and angsty, so this one will be predominantly fluff. I hope you enjoy it!

Nothing in Dean Winchester’s life has ever been exceptionally unprecedented. 

There was literally no action, nothing new or exciting to catch him off guard. He lived in the middle of Kansas; of course nothing interesting happened here. 

Until, of course, the Milton family moved into town four years ago. 

As Dean slumped forward against his desk, preparing himself mentally for the drone of Mr. Crowley’s history lesson, the classroom door thudded hard against the wall beside it. It’d swung open, and swung open HARD. Standing in the doorway was the most beautiful boy Dean had ever seen. Years after his first dramatic entrance into his freshman English course, he still held his breathe at the sight of this smirking boy. 

“Castiel, I presume. Your reputation precedes you.” 

Crowley's smug drawl didn't carry the same bite it usually did; then again, everything seemed to just be buzzing in the background of Castiel. 

He strode into the classroom, tussled black hair looking as destructive as ever. His skinny jeans hugged his legs and the black long-sleeved t-shirt clung onto his body like another layer of skin. Doc Martens clicked against the ground, tied tightly over the ends of the pant legs. Eyeliner coated the circumference of his expressive blue eyes, making them appear electric. His presence brought with it a certain thickness in the air, and Dean was suddenly having trouble breathing because of it. Dean looked onward, staring while trying not to stare. He knew it was a losing battle; for the past four years, he’d stared every time Cas entered a room. 

Castiel Milton is a walking enigma, and there was no force on earth that could break the gravitational pull between Dean’s eyes and this boy. 

Dean’s gaze followed Castiel all the way to the back of the classroom, and he knew that this boy was intoxicating, addicting, invigorating even. 

“God,” Dean thought, “he is starlight.” Air blew from his lips as Castiel sat down in the vacant seat. Dean blinked a few times, reeling in his stare... Until he noticed Cas was staring back. 

His stomach constricted and he took a sharp inhale of breath, turning away at lightning speed. He heard a lightly, rumbling chuckle from the back of the classroom as Crowley began explaining the finer points of essay writing. Risking a backward glance, Dean made eye contact with Castiel. Castiel's unbearably blue eyes glimmered with mischief, the permanent smirk twitching into more of a smug grin. Dean blinked, surprised by the sudden attention from this beautiful boy. 

Then, without warning, Castiel winked at him.

Heat rose from Dean's neck, this unexpected act taking him completely off guard.

Dean, stirred and furiously blushing, push himself out of his seat and, after quickly gathering his things, raced out of the classroom. Behind him, a throaty laugh echoed against the sound of his teacher's demands for him to come back. 

He didn't turn back. After years of hopeless pining after Cas, that was too much to handle. If he hadn't walked out right then, he would have hyperventhilated until his throat constricted completely. 

Dean's feelings for Castiel had surpassed that of a crush, and of a liking, and maybe even desperate obsession. Who knew you could fall so completely for someone without having shared even a dozen words with them?

God, he was fucked.


	2. Chapter 2

**Summary for the Chapter:**

> Dean stumbles through life, lost in thought, waiting for English to roll around.

Dean Winchester drove to school on Tuesday in a haze, mind wandering to the previous day over and over again. Could he face English class today?

Mr. Crowley had called home, and his mother and father had made it clear enough that running away from your problems wouldn’t make them go away. While he knew this, they didn’t realize that he wasn’t running away from English homework or petty educational problems. He was smart, he could take any curve ball his teachers threw and knock their teeth in with it.

What he couldn’t take, however, was the boy he’d been secretly crushing on for the entirely of high school flirting very obviously with him after three and a half years of dismissing his entire existence. It was too much, especially now that there was nothing to be done about it. A few months from now is graduation, and there was no time to deal with relationships, friendships, college arrangements and exams. He could only handle so much, really.

Wait, what am I thinking? Dean thought, shaking his head incredulously. It was a wink, not a marriage proposal. Calm down, it probably meant nothing to him.

But it meant everything to you. His inner voice murmured in the back of his mind, urging him to make a move or do anything at all.

Sam was chattering away in the passenger seat about some chick named Jessica, trying to get some advice from his big brother. But Dean couldn’t find it within himself to listen right now. There were more important things to deal with than his baby brother’s freshman crush.

He’ll probably hear about it again from Sam on the drive home anyway.

-

Once he parked his Baby and shoved his books into his locker, Dean made his way to his ever-charming group of friends. The magnificent gang of geeks were nestled up in the stairway entry as they usually were, propping themselves up against the walls on either side of them.

Benny, Charlie, Jo and Adam sat laughing furiously over something Charlie was now miming out. From the looks of it, it was something from Doctor Who earlier that weekend. Jo’s hand was wrapped up in Charlie’s, the ever-cute lesbian couple continuing their traditional minor PDA. Benny and Adam were clutching each other to remain standing, backs pressed against the wall in a futile effort to regain their balance.

He joins his friends physically, but not mentally. For Dean, the world has stopped. It’s zeroed in on him and Castiel, yesterday morning in English class. He sees Cas again, all gorgeous eyes and long legs. His hair looks unruly and untameable as per usual, and it’s perfect chaos. Castiel looks like sex on legs, an angel kicked out of heaven, and he was staring back at him. Castiel was staring back at Dean.

A smile broke through his daydream and planted itself firmly on his face. Maybe, just maybe, he was supposed to act on that impulsive desire to kiss the smug smirk of off Castiel’s beautiful face. Perhaps this is how Castiel’s kind calls for its mates; through teasing and temptations, making them crawl to you.

Sure, maybe it was nothing. Castiel was the type to flirt senselessly, and for no good reason at all. He's been kissing girls near-constantly for years, even though he's not really into girls. A wink to him would be like a glance from anybody else, but senior year was almost over. 

It's been said that senior year is the time to take chances. Maybe, just maybe, Castiel is a mistake Dean needs to make. 

The bell screamed in his ear, pulling him out of his dream with a harsh twang that marked the beginning of class.

Dean made his way through the halls to his locker, and then approached his English classroom. Today was the day, and nothing could change his mind about that.

**Notes for the Chapter:**

> Somewhat short, but I have a massive chapter that'll be posted once I edit it a bit. 
> 
> Hope you guys like it so far. Stay tuned; things are about to get good. 
> 
> Twitter: @billyteddytrash  
> Tumblr: billyteddytrash  
> Comments and kudos are appreciated!


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